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Synthesis of (±)‐Trinervitadiene‐2,3‐diol
Author(s) -
Kato Tadahiro,
Hoshikawa Masahiro
Publication year - 2004
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.200490086
Subject(s) - chemistry , epoxide , diol , skeleton (computer programming) , bicyclic molecule , ring (chemistry) , stereochemistry , combinatorial chemistry , organic chemistry , catalysis , programming language , computer science
The first synthesis of trinervita‐1(15),8(19)‐dien‐2 β ,3 α ‐diol ( 2a ) and its 2 α ‐isomer 2b , which have been isolated from termite soldiers, where they are used as defense chemicals, is documented starting from geranylgeranioic acid in 33 steps. The route for construction of the key intermediate of the trinervitane skeleton 8 has been developed previously ( Scheme 1 ). Noteworthy features include the efficient construction of the trinervitane framework from the corresponding bicyclic 7(16)‐secotrinervitane skeleton and Me 3 SiCl (TMSCl)‐induced ring‐opening of tetrasubstituted epoxide to give the corresponding allyl alcohols ( Scheme 7 ). The synthetic route developed in the present study seems applicable to the syntheses of other trinervitane‐type natural products.